54810-34-3

Basic information

• Product Name: 5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL
• Synonyms: TIMTEC-BB SBB010704;5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL
• CAS NO: 54810-34-3
• Molecular Formula: C9H10ClNO
• Molecular Weight: 183.63
• Mol File: 54810-34-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 116-117 °C
• Boiling Point: 329.7±42.0 °C(Predicted)
• Appearance: /
• Density: 1.287±0.06 g/cm3(Predicted)
• PKA: 10.71±0.20(Predicted)
• CAS DataBase Reference: 5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL(54810-34-3)
• EPA Substance Registry System: 5-CHLORO-1,2,3,4-TETRAHYDRO-QUINOLIN-8-OL(54810-34-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 54810-34-3(Hazardous Substances Data)

Upstream product

• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 6640-50-2 1,2,3,4-tetrahydroquinolin-8-ol 

Relevant articles and documents

Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

Selective N-cycle hydrogenation of quinolines with sodium borohydride in aqueous media catalyzed by hectorite-supported ruthenium nanoparticles: Dedicated to Professor Heinrich Lang on the occasion of his 60th birthday

A new catalyst containing metallic ruthenium nanoparticles intercalated in hectorite (nanoRu'@hectorite) was found to catalyze the reduction of quinoline and quinoline derivatives by NaBH4in aqueous solution to give selectively the corresponding 1,2,3,4-tetrahydroquinolines (N-cycle hydrogenation). In most cases the reaction can be done under mild conditions (25–60 °C) without pressure equipment, conversion and selectivity being superior to 99%. In the case of sterically hindered derivatives, the reaction can be done in a pressure vessel under self-generated pressure (up to 9 bar). Isoquinoline and quinoxalines also undergo selective N-cycle hydrogenation, but 2-phenyl-quinoline is hydrogenated to give 2-phenyl-5,6,7,8-tetrahydroquinoline (C-cycle hydrogenation). Isotope labeling experiments combined with semi-empirical calculations of the electrostatic potentials support a heterolytic hydrogenation mechanism involving a hydride from NaBH4and a proton from H2O. The catalyst nanoRu'@hectorite can be recycled and reused.

Substituted benzoxazine derivatives and fungicidal use

Novel Substituted benzoxazine derivatives of the formula STR1 in which X is oxygen or suophur, and R1 and R2 each independently is hydrogen, alkyl, alkoxy, akylthio, halogenoalkyl, alkanoyl, aroyl, halogen, cyano, nitro, nitroso, amino or the suophonic acid grouping, with the restriction that either of R1 and R2 does not represent hydrogen if the other represents hydrogen, the 6-methyl group, the 6-ethyl group, the 6-butyl group or the 6-acetyl group and X is oxygen, which possess fungicidal activity. A few related compounds, though known, also possess such activity.